Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

Wanli Zhang; Anna R Kaplan; Emma K Davison; Jared L Freeman; Margaret A Brimble; William M Wuest

doi:10.1039/d0np00052c

Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

Nat Prod Rep. 2021 May 26;38(5):880-889. doi: 10.1039/d0np00052c.

Authors

Wanli Zhang¹, Anna R Kaplan¹, Emma K Davison², Jared L Freeman³, Margaret A Brimble², William M Wuest⁴

Affiliations

¹ Department of Chemistry, Emory University, USA. wwuest@emory.edu.
² School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland, 1010, New Zealand and School of Biological Sciences, University of Auckland, 23 Symonds St., Auckland, 1010, New Zealand and The Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland, 1142, New Zealand.
³ School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland, 1010, New Zealand and The Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland, 1142, New Zealand.
⁴ Department of Chemistry, Emory University, USA. wwuest@emory.edu and Emory Antibiotic Resistance Center, Emory School of Medicine, USA.

Abstract

Covering: 2000 to 2020. trans-Bicyclo[4.4.0]decane/decene (such as trans-decalin and trans-octalin)-containing natural products display a wide range of structural diversity and frequently exhibit potent and selective antibacterial activities. With one of the major factors in combatting antibiotic resistance being the discovery of novel scaffolds, the efficient construction of these natural products is an attractive pursuit in the development of novel antibiotics. This highlight aims to provide a critical analysis on how the presence of dense architectural and stereochemical complexity necessitated special strategies in the synthetic pursuits of these natural trans-bicyclo[4.4.0]decane/decene antibiotics.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Review

MeSH terms

Alkanes / chemical synthesis*
Anti-Bacterial Agents / chemical synthesis*
Biological Products
Bridged Bicyclo Compounds / chemical synthesis*
Molecular Structure

Substances

Alkanes
Anti-Bacterial Agents
Biological Products
Bridged Bicyclo Compounds
decane

Grants and funding

R35 GM119426/GM/NIGMS NIH HHS/United States